Antifoulant compositions for vapor-space applications

Abstract

Polymerization inhibitor compositions are provided. The polymerization inhibitor compositions include at least a first inhibitor compound including a hydroxylamine, a second inhibitor including phenylenediamine, and a third inhibitor including a benzoquinone or naphthoquinone. Methods of inhibiting the polymerization of monomers using the compositions of the disclosure are also provided. The methods of inhibiting polymerization of monomers include a step of adding a composition of the disclosure to the monomer. In some instances, the monomer is an ethylenically unsaturated monomer. Such ethylenically unsaturated monomers include, but are not limited to, vinyl acetate, acrylonitrile, acrylates, methacrylates, 1,3-butadiene, styrene, isoprene, (meth)acrylic acid, and combinations thereof. Methods of preparing the polymerization inhibitors and compositions of the disclosure are also provided.

What is claimed is: 
     
       1. A composition for inhibiting monomer polymerization consisting essentially of:
 a first inhibitor compound comprising a hydroxylamine; 
 a second inhibitor compound comprising a phenylenediamine; and 
 a third inhibitor compound comprising a benzoquinone or naphthoquinone. 
 
     
     
       2. The composition of  claim 1 , wherein the first inhibitor compound is of formula (II): 
       
         
           
           
               
               
           
         
         wherein R 2  is C 1 -C 22  alkyl, C 1 -C 22  alkenyl, C 1 -C 22  alkynyl, C 1 -C 22  cycloalkyl, aryl, —C 1 -C 22  alkylene, —C(O)(C 1 -C 22  alkyl), —C(O)(C 1 -C 22  alkenyl), —C(O)(C 1 -C 22  alkynyl), —C(O)(C 1 -C 22  cycloalkyl), —C(O)(aryl), or —C(O)(C 1 -C 22  alkylene), wherein the alkyl, alkylene, cycloalkyl, and aryl are optionally substituted with one or more C 1 -C 22  alkyl, C 1 -C 22  alkenyl, C 1 -C 22  alkynyl, or aryl. 
       
     
     
       3. The composition of  claim 1 , wherein R 2  is —C(O)(C 1 -C 22  alkyl), —C(O)(C 1 -C 22  alkenyl), —C(O)(C 1 -C 22  alkynyl), —C(O)(C 1 -C 22  cycloalkyl), —C(O)(aryl), or —C(O)(C 1 -C 22  alkylene), wherein the alkyl, alkylene, cycloalkyl, and aryl are optionally substituted with one or more C 1 -C 22  alkyl, C 1 -C 22  alkenyl, C 1 -C 22  alkynyl, or aryl. 
     
     
       4. The composition of  claim 1 , wherein the first inhibitor is selected from the group consisting of: 2,2,6,6-tetramethylpiperin-1,4-diol; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-ethoxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-propoxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-butoxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-pentoxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-hexyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-heptyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-octyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-nonyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-decyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-undecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-dodecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-tridecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-tetradecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-pentadecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-hexadecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-heptadecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-octadecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-nodecyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-decyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-icosyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-henicosyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-docosyloxy-2,2,6,6-tetramethylpiperidin-1-ol; 4-(phenoxy)-2,2,6,6-tetramethylpiperidin-1-ol; 4-(benzyloxy)-2,2,6,6-tetramethylpiperidin-1-ol; 2,2,6,6-tetramethyl-4-(naphthalen-2-yloxy)piperidin-1-ol; and any combination thereof. 
     
     
       5. The composition of  claim 1 , wherein the first inhibitor is a compound of formula IIa: 
       
         
           
           
               
               
           
         
         wherein R 4  is H, C 1 -C 22  alkyl, C 1 -C 22  alkenyl, C 1 -C 22  alkynyl, C 1 -C 22  cycloalkyl, aryl, —C 1 -C 22  alkylene, —C(O)(C 1 -C 22  alkyl), —C(O)(C 1 -C 22  alkenyl), —C(O)(C 1 -C 22  alkynyl), —C(O)(C 1 -C 22  cycloalkyl), —C(O)(aryl), or —C(O)(C 1 -C 22  alkylene), wherein the alkyl, alkylene, cycloalkyl, and aryl are optionally substituted with one or more C 1 -C 22  alkyl, C 1 -C 22  alkenyl, C 1 -C 22  alkynyl, or aryl. 
       
     
     
       6. The composition of  claim 5 , wherein the first inhibitor is selected from the group consisting of: 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl acetate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl propanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl butyrate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl pentanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl hexanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl heptanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl octanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl nonanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl decanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ylundecanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl dodecanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl 2-ethylhexanoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl stearate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl benzoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl palmitoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl behenoate, 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl 4-tert-butylbenzoate, or any combination thereof. 
     
     
       7. The composition of  claim 1 , wherein the second inhibitor compound is a phenylenediamine of formula (IV) or formula (V): 
       
         
           
           
               
               
           
         
         wherein X 1  and X 2  are independently C 1 -C 22  alkyl, or aryl, wherein the alkyl and aryl are optionally substituted with one or more C 1 -C 22  alkyl or aryl. 
       
     
     
       8. The composition of  claim 1 , wherein the second inhibitor is selected from the group consisting of: 1,2-phenylenediamine, 1,4-phenylenediamine, N,N′-di-methyl-p-phenylenediamine, N,N′-di-sec-butyl-1,4-phenylenediamine, N,N′-di-1,4-dimethylpentyl-1,4-phenylenediamine, N,N′-di-ethyl-1,4-phenylenediamine, N-tert-butyl-N′-phenyl-1,4-phenylenediamine, N,N′-di-phenyl-1,4-phenylenediamine, and any combination thereof. 
     
     
       9. The composition of  claim 1 , wherein the third inhibitor compound is a benzoquinone of formula (VI) or formula (VII): 
       
         
           
           
               
               
           
         
         wherein X 3 , X 4 , X 5 , and X 6  are independently H, C 1 -C 22  alkyl, or aryl, wherein the alkyl and aryl are optionally substituted with one or more C 1 -C 22  alkyl or aryl. 
       
     
     
       10. The composition of  claim 1 , wherein the third inhibitor compound is a naphthoquinone of formula (VII) or formula (VIII): 
       
         
           
           
               
               
           
         
         wherein X 5  and X 6  are independently H, C 1 -C 22  alkyl, aryl, wherein the alkyl and aryl are optionally substituted with one or more C 1 -C 22  alkyl or aryl. 
       
     
     
       11. The composition of  claim 1 , wherein the first inhibitor compound is present in the composition at a concentration of about 0.01% by weight to about 80% by weight, and the second inhibitor compound is present in the composition at a concentration of about 0.01% by weight to about 50% by weight. 
     
     
       12. The composition of  claim 1 , wherein the composition further comprises an organic solvent. 
     
     
       13. The composition of  claim 1 , wherein the composition further comprises an ethylenic unsaturated monomer selected from the group consisting of vinyl acetate, acrylonitrile, an acrylate, a methacrylate, 1,3-butadiene, styrene, isoprene, acrylic acid, methacrylic acid and any combination thereof. 
     
     
       14. A method of inhibiting polymerization of a monomer, the method comprising:
 adding the composition of  claim 1  to the monomer. 
 
     
     
       15. The method of  claim 14 , wherein the monomer is provided within a solution. 
     
     
       16. The method of  claim 15 , wherein the solution further comprises one or more additional components selected from: an acid, an organic solvent, and water. 
     
     
       17. The method of  claim 14 , wherein the monomer is an ethylenic unsaturated monomer. 
     
     
       18. The method of  claim 14 , wherein the composition is added to the monomer such that a concentration of the first inhibitor compound is about 0.1 ppm to about 10,000 ppm. 
     
     
       19. The method of  claim 14 , wherein the composition is added to the monomer such that a concentration of the second inhibitor compound is about 0.1 ppm to about 10,000 ppm.